#------------------------------------------------------------------------------
#$Date: 2009-11-16 02:43:51 +0100 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008975.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2008975
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_journal_page_first  1519
_journal_page_last  1522
_publ_section_title
;
Methyl 1-(4-chlorobenzyl)-2-oxocyclohexane-1-carboxylate and methyl
(2RS,4aRS,8aRS)-2-(4-chlorobenzyl)-3-oxoperhydronaphthalene-2-carboxylate
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
loop_
_publ_author_name
  'H. Surya Prakash Rao'
  'S. Rajamathe'
  'S. Shanmuga Sundara Raj'
  'Kandasamy Chinnakali'
  'Ibrahim Abdul Razak'
  'Hoong-Kun Fun'
_chemical_formula_sum  'C19 H23 Cl O3'
_chemical_formula_weight  334.82
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x-1/2, -y-1/2, z-1/2'
_cell_length_a  11.7762(3)
_cell_length_b  11.8495(4)
_cell_length_c  13.0464(4)
_cell_angle_alpha  90.00
_cell_angle_beta  102.9050(10)
_cell_angle_gamma  90.00
_cell_volume  1774.54(9)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.253
_diffrn_ambient_temperature  293(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  Cl1 0.94513(7) 0.19570(6) 0.05568(6) 0.0825(3) Uani d . 1 . . Cl
  O1 1.15544(16) -0.14810(17) -0.50176(14) 0.0774(5) Uani d . 1 . . O
  O2 1.07261(15) -0.26151(13) -0.30171(16) 0.0748(5) Uani d . 1 . . O
  O3 0.96194(13) -0.12059(13) -0.38256(14) 0.0649(5) Uani d . 1 . . O
  C1 1.26350(16) -0.11919(15) -0.22959(15) 0.0414(5) Uani d . 1 . . C
  H1A 1.2387 -0.1009 -0.1655 0.050 Uiso calc R 1 . . H
  H1B 1.2734 -0.2004 -0.2312 0.050 Uiso calc R 1 . . H
  C2 1.16601(17) -0.08436(15) -0.32450(15) 0.0409(4) Uani d . 1 . . C
  C3 1.2123(2) -0.09951(18) -0.42588(17) 0.0498(5) Uani d . 1 . . C
  C4 1.3317(2) -0.0533(2) -0.42320(18) 0.0594(6) Uani d . 1 . . C
  H4A 1.3279 0.0284 -0.4247 0.071 Uiso calc R 1 . . H
  H4B 1.3562 -0.0779 -0.4858 0.071 Uiso calc R 1 . . H
  C5 1.5435(2) -0.0404(2) -0.3232(2) 0.0707(8) Uani d . 1 . . C
  H5A 1.5695 -0.0641 -0.3853 0.085 Uiso calc R 1 . . H
  H5B 1.5381 0.0413 -0.3244 0.085 Uiso calc R 1 . . H
  C6 1.6326(2) -0.0772(2) -0.2254(2) 0.0801(9) Uani d . 1 . . C
  H6A 1.7063 -0.0397 -0.2237 0.096 Uiso calc R 1 . . H
  H6B 1.6451 -0.1579 -0.2282 0.096 Uiso calc R 1 . . H
  C7 1.5909(2) -0.0483(3) -0.1261(2) 0.0817(9) Uani d . 1 . . C
  H7A 1.6469 -0.0758 -0.0651 0.098 Uiso calc R 1 . . H
  H7B 1.5858 0.0331 -0.1199 0.098 Uiso calc R 1 . . H
  C8 1.4721(2) -0.1006(2) -0.12838(19) 0.0610(6) Uani d . 1 . . C
  H8A 1.4465 -0.0786 -0.0656 0.073 Uiso calc R 1 . . H
  H8B 1.4789 -0.1822 -0.1283 0.073 Uiso calc R 1 . . H
  C9 1.38132(16) -0.06328(16) -0.22555(15) 0.0423(5) Uani d . 1 . . C
  H9A 1.3714 0.0186 -0.2218 0.051 Uiso calc R 1 . . H
  C10 1.42318(18) -0.09038(18) -0.32614(16) 0.0486(5) Uani d . 1 . . C
  H10A 1.4304 -0.1726 -0.3298 0.058 Uiso calc R 1 . . H
  C11 1.12850(18) 0.04199(16) -0.31982(16) 0.0442(5) Uani d . 1 . . C
  H11A 1.1952 0.0893 -0.3218 0.053 Uiso calc R 1 . . H
  H11B 1.0690 0.0583 -0.3825 0.053 Uiso calc R 1 . . H
  C12 1.08193(17) 0.07506(15) -0.22428(16) 0.0422(5) Uani d . 1 . . C
  C13 1.15759(19) 0.10394(17) -0.12943(17) 0.0478(5) Uani d . 1 . . C
  H13A 1.2376 0.0999 -0.1240 0.057 Uiso calc R 1 . . H
  C14 1.1158(2) 0.13872(18) -0.04283(18) 0.0544(6) Uani d . 1 . . C
  H14A 1.1672 0.1569 0.0201 0.065 Uiso calc R 1 . . H
  C15 0.9972(2) 0.14580(17) -0.05155(19) 0.0543(6) Uani d . 1 . . C
  C16 0.9202(2) 0.11839(18) -0.1441(2) 0.0597(6) Uani d . 1 . . C
  H16A 0.8403 0.1233 -0.1491 0.072 Uiso calc R 1 . . H
  C17 0.96299(19) 0.08328(18) -0.23001(19) 0.0541(6) Uani d . 1 . . C
  H17A 0.9109 0.0650 -0.2925 0.065 Uiso calc R 1 . . H
  C18 1.06355(19) -0.16603(18) -0.33362(18) 0.0499(5) Uani d . 1 . . C
  C19 0.8609(2) -0.1937(2) -0.3959(3) 0.0877(9) Uani d . 1 . . C
  H19A 0.7917 -0.1507 -0.4235 0.131 Uiso calc R 1 . . H
  H19B 0.8565 -0.2253 -0.3292 0.131 Uiso calc R 1 . . H
  H19C 0.8676 -0.2534 -0.4440 0.131 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  Cl1 0.1037(6) 0.0776(5) 0.0828(5) 0.0114(4) 0.0563(4) 0.0021(4)
  O1 0.0701(12) 0.1066(14) 0.0504(10) 0.0037(10) 0.0022(9) -0.0215(10)
  O2 0.0619(11) 0.0439(9) 0.1138(16) -0.0070(8) 0.0096(10) 0.0089(9)
  O3 0.0424(9) 0.0547(9) 0.0912(13) -0.0011(7) 0.0017(9) -0.0038(9)
  C1 0.0437(12) 0.0380(10) 0.0441(12) 0.0035(8) 0.0131(9) 0.0015(8)
  C2 0.0410(11) 0.0367(10) 0.0445(12) 0.0020(8) 0.0085(9) 0.0017(8)
  C3 0.0540(13) 0.0511(12) 0.0426(12) 0.0097(10) 0.0073(10) 0.0017(10)
  C4 0.0698(16) 0.0626(14) 0.0522(14) -0.0003(12) 0.0273(12) 0.0055(11)
  C5 0.0619(16) 0.0675(16) 0.092(2) -0.0160(13) 0.0367(16) -0.0136(14)
  C6 0.0429(14) 0.0861(19) 0.112(2) -0.0121(13) 0.0194(15) -0.0336(17)
  C7 0.0473(15) 0.098(2) 0.092(2) 0.0021(14) -0.0007(14) -0.0308(17)
  C8 0.0503(14) 0.0714(16) 0.0575(14) 0.0086(12) 0.0035(11) -0.0100(12)
  C9 0.0397(11) 0.0389(10) 0.0485(12) 0.0015(8) 0.0103(9) -0.0049(9)
  C10 0.0461(12) 0.0470(11) 0.0556(14) -0.0052(9) 0.0178(11) -0.0055(10)
  C11 0.0451(12) 0.0393(10) 0.0472(12) 0.0026(9) 0.0080(9) 0.0041(9)
  C12 0.0438(12) 0.0316(10) 0.0512(13) 0.0047(8) 0.0104(10) 0.0050(9)
  C13 0.0426(12) 0.0455(11) 0.0544(13) 0.0080(9) 0.0090(10) 0.0015(10)
  C14 0.0610(15) 0.0524(13) 0.0483(13) 0.0118(11) 0.0086(11) 0.0032(10)
  C15 0.0627(15) 0.0425(11) 0.0659(15) 0.0048(11) 0.0316(13) 0.0072(11)
  C16 0.0443(13) 0.0520(13) 0.0878(18) -0.0003(10) 0.0251(13) -0.0021(12)
  C17 0.0446(13) 0.0479(12) 0.0674(16) 0.0014(10) 0.0071(11) -0.0045(11)
  C18 0.0467(13) 0.0425(12) 0.0596(14) 0.0004(9) 0.0098(11) -0.0079(10)
  C19 0.0468(15) 0.0789(19) 0.131(3) -0.0112(13) 0.0071(16) -0.0139(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  Cl1 C15 . 1.751(2) y
  O1 C3 . 1.210(3) y
  O2 C18 . 1.202(2) y
  O3 C18 . 1.337(3) y
  O3 C19 . 1.451(3) y
  C1 C9 . 1.528(3) ?
  C1 C2 . 1.545(3) ?
  C2 C18 . 1.530(3) yes
  C2 C3 . 1.549(3) yes
  C2 C11 . 1.566(3) ?
  C3 C4 . 1.502(3) ?
  C4 C10 . 1.532(3) ?
  C5 C6 . 1.523(4) ?
  C5 C10 . 1.528(3) ?
  C6 C7 . 1.524(4) ?
  C7 C8 . 1.524(3) ?
  C8 C9 . 1.530(3) ?
  C9 C10 . 1.535(3) ?
  C11 C12 . 1.521(3) ?
  C12 C17 . 1.389(3) ?
  C12 C13 . 1.396(3) ?
  C13 C14 . 1.392(3) ?
  C14 C15 . 1.379(3) ?
  C15 C16 . 1.377(3) ?
  C16 C17 . 1.392(3) ?